Synthesis of β-sulfanyl ketones via a tandem rearrangement-conjugate addition reaction catalyzed by a Re(V)-oxo complex

被引：3

作者：

Garst, Alyson E. ^{[1
]}

Badiceanu, Alexandra D. ^{[1
]}

Nolin, Kristine A. ^{[1
]}

机构：

[1] Univ Richmond, Dept Chem, Richmond, VA 23173 USA

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 06期

关键词：

Sulfanyl ketone; Conjugate addition; Rearrangement; Catalytic; Rhenium; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; MEYER-SCHUSTER REARRANGEMENT; THIA-MICHAEL ADDITION; PROMOTED CLEAVAGE; HIGHLY EFFICIENT; ENONES; THIOLS; ACID; DERIVATIVES; DISULFIDES;

D O I：

10.1016/j.tetlet.2012.11.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for synthesizing beta-sulfanyl ketones via a tandem rearrangement and conjugate addition reaction has been developed. This methodology provides access to a range of beta-sulfanyl ketones through the rearrangement of propargyl alcohols to the corresponding enones followed by the conjugate addition of unactivated thiols. The one-pot, tandem transformation is catalyzed by ReOCl3(OPPh3)(S(CH3)(2)) affording aryl and alkyl beta-sulfanyl ketones in good to excellent yield. (C) 2012 Elsevier Ltd. All rights reserved.

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页码：459 / 461

页数：3

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